Can't recover files from iTunes, AND had no opportunity to backup...

Hi everyone!
I've been helping my (non-media-suave) father re-sync his iPhone to his PC, after it was reformatted. We were re-adding his music from the phone, and couldn't figure out why they weren't being added to the PC. We tried checking the "Sync Music" box, and that came up with a "Do you want to replace the music on the iPhone with the music on the PC?" dialog box. Without a chance for me to intervene, he clicked "Sync and erase".
So, long story short, I need to help get his music back, in a situation with no relation to the backup system, as we had lost them before they were on the PC.
Any help/directions would be appreciated. Thanks!

If you didn't make a back-up of the music/movie purchases to restore from (as you are advised to do) then I'm sorry to say that I'm sorry to say that the policy on lost music/media purchases is that you only get one download: iTunes Store: Purchased content can be downloaded only once
The licensing of Purchased applications allows for them be downloaded over again, see this article for details: How to redownload purchased applications from the App Store
You could try contacting iTunes Store Customer Service and you might be able to persuade them to sanction a second free download. There have been occasional reports in the iTunes forum of this happening, however just be aware that they are not under any obligation to do so. If you click on this link it'll take you to the support/contact page, from there click on Music Purchases then the Lost or Missing Items option, from there click on "Email Us": Customer Service - iTunes Store Support
You might also want to check out these pages for future reference:
How to back up your media in iTunes
Back up your iTunes library by copying to an external hard drive

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